US4761181A - Method for stabilizing organic base substances to light - Google Patents

Method for stabilizing organic base substances to light Download PDF

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US4761181A
US4761181A US07/006,364 US636487A US4761181A US 4761181 A US4761181 A US 4761181A US 636487 A US636487 A US 636487A US 4761181 A US4761181 A US 4761181A
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organic base
dyes
light
base substance
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Yoshiaki Suzuki
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Fujifilm Corp
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Fuji Photo Film Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/0091—Complexes with metal-heteroatom-bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
    • C07F15/02—Iron compounds
    • C07F15/025—Iron compounds without a metal-carbon linkage
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
    • C07F15/04—Nickel compounds
    • C07F15/045—Nickel compounds without a metal-carbon linkage
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C7/00—Multicolour photographic processes or agents therefor; Regeneration of such processing agents; Photosensitive materials for multicolour processes
    • G03C7/30—Colour processes using colour-coupling substances; Materials therefor; Preparing or processing such materials
    • G03C7/392—Additives
    • G03C7/39208—Organic compounds
    • G03C7/39284—Metallic complexes

Definitions

  • This invention relates to stabilization of organic base substances to light.
  • organic base substances e.g. organic dyes
  • organic base substances e.g. organic dyes
  • azomethine dyes or indoaniline dyes are formed by reaction between oxidants of aromatic primary amine photographic developers and couplers as is particularly set forth in Chapter 17 of "The Theory of the Photographic Process, by C. E. Mees and T. H. James (Macmillan Pub. 1967)".
  • a number of methods of improving light stability of images formed from these dyes or color images are known. For instance, there are known methods using hydroquinone derivatives as described in U.S. Pat. Nos. 2,360,290, 2,418,613, 2,675,314, 2,701,197, 2,704,713, 2,728,659, 2,732,300, 2,735,765, 2,710,801 and 2,816,028 and British Pat. No.
  • 1,363,921 gallic acid derivatives as described in U.S. Pat. Nos. 3,457,079 and 3,069,262 and Japanese Patent Publication No. 13,496/1968, p-alkoxyphenols as described in U.S. Pat. Nos. 2,735,765 and 3,698,909, and derivatives such as chroman and coumaran as described in U.S. Pat. Nos. 3,432,300, 3,573,050, 3,574,627, 3,764,337, 3,574,626, 3,698,909 and 4,015,990.
  • these compounds serve, more or less, as an inhibitor for fading or discoloration of color images but are not satisfactory.
  • British Pat. No. 1,451,000 describes a method of improving light stability of an organic base compound by the use of azomethine extinction compounds whose absorption maximum is larger than an absorption maximum of the organic base compound.
  • this method is disadvantageous in that because the azomethine extinction compound is deeply colored, it greatly influences the hue of the base compound.
  • An object of the invention is to provide a method for improving light stability of organic base substances.
  • Another object of the invention is to provide a method for improving light stability of organic base substances and, particularly, dyestuffs or dyes without deterioration of their hue and purity.
  • a further object of the invention is to provide a method for improving light stability of organic infrared-absorptive substances.
  • a still further object of the invention to provide a method for improving light stability of organic base substances by the use of stabilizers for such organic base substances which have high solubility in organic solvent and a high miscibility with the organic base substances.
  • the present inventors made extensive studies in order to achieve the above objects and, as a result, have accomplished the method of the invention.
  • the above objects can be attained by comprising an organic base substance having an absorption maximum at about 300 nm to about 1,500 nm in coexistence with at least one compound of the following general formula (I) or (II) ##STR1## in which [Cat 1 ] and [Cat 2 ] represent, respectively, a cation necessary for neutralizing the complex, M 1 and M 2 represent, respectively, nickel, copper, palladium or platinum, and n is 1 or 2.
  • the method of the invention is very effective for the purpose of improving the fastness of organic base substances to light.
  • organic base substance or “base compound” used herein is intended to mean substances which are visually observed as colored or colorless under irradiation of sunlight. More particularly, the substances include not only those substances which have an absorption maximum merely in a visible range, but also optical fluorescent brighteners or substances having an absorption maximum in an IR region. In the practice of the invention, the organic base substances also include organic substances whose absorption maximum ranges from about 300 nm in a UV region to about 1,500 nm in an IR region.
  • dye used herein includes color materials and dyestuffs and is intended to mean organic substances which are visually observed as colored under sunlight.
  • the term "light” used herein is intended to mean an electromagnetic wave of less than about 1,500 nm, which includes an UV ray of less than about 400 nm, visible light of from 400 nm to about 700 nm, and an IR ray of from about 700 nm to about 1,500 nm.
  • the cations represented by [Cat 1 ] and [Cat 2 ] may be inorganic cations which include alkali metals such as, for example, Li, Na, K and the like, alkaline earth metals such as Mg, Ca, Ba and the like, and NH 4 + .
  • Organic cations may also be used including a quaternary ammonium ion and a quaternary phosphonium ion.
  • preferable cations are those of the following general formulae (III-a), (III-b), (III-c), (III-d) and (III-e).
  • R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 10 , R 11 and R 12 independently represent a substituted or unsubstituted alkyl group having from 1 to 20 carbon atoms or a substituted or unsubstituted aryl group having from 6 to 14 carbon atoms
  • Z 1 and Z 2 independently represent a non-metallic atom group to form a five-membered or six-membered ring along with a nitrogen atom in the respective formulae.
  • Examples of the substituted or unsubstituted alkyl group having from 1 to 20 carbon atoms include a methyl group, an ethyl group, an n-butyl group, an iso-amyl group, an n-dodecyl group, an n-octadecyl group and the like.
  • Examples of the aryl group having from 6 to 14 carbon atoms include a phenyl group, a tolyl group, an alpha-naphthyl group and the like.
  • alkyl groups or aryl groups may be further substituted with a cyano group a hydroxyl group, an alkyl group having from 1 to 20 carbon atoms (for example, a methyl group, an ethyl group, an n-butyl group, an n-octyl group or the like) an aryl group having from 6 to 14 carbon atoms (for example, a phenyl group, a tolyl group, an alpha-naphthyl group or the like) an acyloxy group having from 2 to 20 carbon atoms (for example, an acetoxy group, a benzoyloxy group, a p-methoxybenzoyloxy group or the like) an alkoxy group having from 1 to 6 carbon atoms (for example, a methoxy group, an ethoxy group, a propoxy group, a butoxy group or the like) an aryloxy group (for example, a phenoxy group, a tolyl
  • Z 1 and Z 2 independently represent a non-metallic atom group necessary for forming a five-membered ring or a six-membered ring.
  • Examples or the five-membered ring and the six-membered ring include a pyridine ring, an imidazole ring, a pyrrole ring, a 2-pyrroline ring, a pyrrolidine ring, a piperidine ring, a pyrazole ring, a pyrazoline ring, an imidazoline ring and the like.
  • the cations represented by the general formula (III-b) are, for example, a dodecylpyridinium group, a hexadecylpyridinium group, a dodecylimidazolium group and the like.
  • the cations represented by the general formula (III-c) are an N-ethyl-N-hexadecylpiperidinium group, an N-ethyl-N-dodecylpirazolinium group and the like.
  • solubility of the compounds of the general formulae [I] and [II] in organic solvents is influenced by the type of cation, e.g. [Cat 1 ] or [Cat 2 ].
  • the solubility becomes higher as the chain length is larger. This tendency becomes more pronounced in the case of tetraalkyl-substituted ammonium or phosphonium. High solubility is ensured in the case of ammonium cations whose carbon atoms are 17 or over in total and phosphonium cations whose carton atoms are 4 or over in total.
  • nickel cobalt, copper, palladium and platinum represented by M 1 and M 2 are preferably used in this order.
  • the metal complexes of the general formulae [I] and [II] have a plane four-coordinate stereostructure. It will be noted that although it is not unconditionally determined whether the thioketone group of the compounds of the general formula [II] is symmetric or asymmetric with respect to the central metal, these compounds are represented in the practice of the invention as by the general formula [II] for convenience' sake.
  • This product is decomposed with an alkali and then reacted with a metal salt to obtain the intended compound.
  • disodium-1,3-dithio-2-thione-4,5-ditholate obtained by reaction between carbon disulfide and sodium for isomerization into disodium-1,2-dithiol-3-thione-4,5-dithiolate.
  • This compound is converted into a zinc complex and reacted with benzoyl chloride to obtain a bisbenzoylthio product.
  • This product is decomposed with an alkali and reacted with a metal salt to obtain the intended compound.
  • the 1,3-dithiol-2-thione-4,5-dithiolate anion which is an intermediate for obtaining the compound of the general formula [I] or [II] may be obtained by electrochemical reduction aside from the above reduction method using Na.
  • the organic base substances according to the invention include substantially all dyes classified as having dyeing properties, e.g. water-soluble dyes such as basic dyes, acid dyes, direct dyes, soluble vat dyes and mordant dyes, insoluble dyes such as sulur dyes, vat dyes oil colors, disperse dyes, azoic dyes and oxidation dyes and reactive dyes.
  • dyeing properties e.g. water-soluble dyes such as basic dyes, acid dyes, direct dyes, soluble vat dyes and mordant dyes, insoluble dyes such as sulur dyes, vat dyes oil colors, disperse dyes, azoic dyes and oxidation dyes and reactive dyes.
  • These organic base substances include not only dyes which are observed as colored under irradiation of sunlight, but also fluorescent brightening dyes which are colorless or light yellow in color.
  • preferable dyes include, upon classification through a chemical structure, quinoneimine dyes such as azine dyes, oxazine dyes, thiazine dyes and the like, methine and polymethine dyes such as cyanine dyes, merocyanine dyes, azomethine dyes and the like, azo dyes, anthraquinone dye, naphthoquinone dyes, indoamine dyes, indoaniline and indophenol dyes, indigoid dyes, carbonium dyes, formazan dyes and the like.
  • quinoneimine dyes such as azine dyes, oxazine dyes, thiazine dyes and the like
  • methine and polymethine dyes such as cyanine dyes, merocyanine dyes, azomethine dyes and the like
  • azo dyes anthraquinone dye, naphthoquinone dyes, ind
  • More preferable dyes used as the organic base substance of the invention include anthraquinone, naphthoquinone, quinoneimineazo, methine, polymethine, azomethine, indoamine, indoaniline, indophenol and formazan dyes.
  • More preferable dyes used in the present invention are anthraquinone, naphthoquinone, quinoneimineazo, methine, polymethine, azomethine, indoamine, indoaniline and indophenol dyes.
  • the metal complexes used in the present invention stabilize organic base substances.
  • the stabilizing effect may be shown when a metal complex and an organic base substance are uniformly dispersed in a suitable medium or binder.
  • Examples of the medium or binder may be polymer substances such as plastic resins.
  • Such polymer substances include, for example, polyesters typical of which is polyethylene terephthalate, cellulose esters such as cellulose diacetate, cellulose triacetate, cellulose acetate butyrate and the like, polyolefins such as polyethylene, polypropylene and the like, polyvinyl compounds such as polyvinyl chloride, polyvinylidene chloride, vinyl chlride-vinyl acetate copolymers, polystyrene and the like, acrylic addition polymers such as polymethyl methacrylate, polycarbonates such as polycarbonic acid esters, phenolic resins, urethane resins, and hydrophilic binders such as gelatin. Preferable mediums or binders are indicated below.
  • Polyolefin copolymers ethylene-vinyl acetate copolymers, ethylene acrylate copolymers, ethylene-acrylic acid copolymers, ethylene-propylene copolymers, ethylene-butene-1 copolymers, ethylene-maleic anhydride copolymers, ethylene-propylene terpolymers (EPT).
  • the ratio of the respective co-monomers may be arbitrarily determined.
  • Vinyl chloride copolymers vinyl acetate-vinyl chloride copolymers, vinyl chloride-vinylidene chloride copolymers, vinyl chloride-maleic anhydride copolymers, copolymers of acrylic esters or methacrylic esters and vinyl chloride, acrylonitrile-vinyl chloride copolymers, vinyl chloride-ether copolymers, copolymers of ethylene or propylene and vinyl chloride, ethylene-vinyl acetate copolymers graft-copolymerized with vinyl chloride and the like.
  • the ratio of monomers for the copolymerization may be arbitrarily determined.
  • Vinylidene chloride copolymers vinylidene chloride-vinyl chloride copolymers, vinylidene chloride-vinyl chloride-acrylonitrile copolymers, vinylidene chloride-butadiene-vinyl halide copolymers, and the like.
  • the ratio of monomers for the copolymerization may be arbitrarily determined.
  • Styrene copolymers styrene-acrylonitrile copolymers (AS resins), styrene-acrylonitrile-butadiene copolymers (ABS resins), styrene-maleic anhydride copolymers (SMA resins), styrene-acrylic ester-acrylamide copolymers, styrene-butadiene copolymer (SBR), styrene-vinylidene chloride copolymers, styrene-methyl methacrylate copolymers, and the like.
  • AS resins styrene-acrylonitrile copolymers
  • ABS resins styrene-acrylonitrile-butadiene copolymers
  • SMA resins styrene-maleic anhydride copolymers
  • SBR styrene-acrylic ester-acrylamide copolymers
  • SBR styrene-
  • the ratio of monomers for the copolymerization may be arbitrarily determined.
  • Styrene type polymers polymers of ⁇ -methylstyrene, p-methylstyrene, 2,5-dichlorostyrene, ⁇ , ⁇ -vinylnaphthalene, ⁇ -vinylpyridine, acenaphthene, vinylanthracene and the like, and copolymers of these monomers such as, for example, copolymers of ⁇ -methylstyrene and methacrylic esters.
  • Terpene resin and picolite a terpene polymer which is a polymer of limonene obtained from ⁇ -pinene and picolite obtained from ⁇ -pinene.
  • Acrylic resins those resins have an atomic group of the following formula are preferred ##STR5## wherein R 21 represents a hydrogen atom or an alkyl group and R 22 represents a substituted or unsubstituted alkyl group. In the above formula, R 21 more specifically represents a hydrogen atom or a lower alkyl group having from 1 to 4 carbon atoms and, preferably, a hydrogen atom or a methyl group.
  • R 22 may be either a substituted or unsubstituted alkyl group.
  • the alkyl group has from 1 to 8 carbon atoms.
  • the substituent should preferably be a hydroxyl group, a halogen atom or an amino group, particularly a dialkylamino group.
  • the atomic group of the above formula may constitute a variety of acrylic resins along with other types of recurring units.
  • acrylic resins are composed of homopolymers or copolymers having recurring units of one or more atomic groups of the above formula.
  • (xii) Acrylonitrile copolymers: acrylonitrile-vinyl acetate copolymers, acrylonitrile-vinyl chloride copolymers, acrylonitrile-styrene copolymers, acrylonitrile-vinylidene chloride copolymers, acrylonitrile-vinylpyridine copolymers, acrylonitrile-methyl methacrylate copolymers, acrylonitrile-butadiene copolymers, acrylonitrile-butyl acrylate copolymers and the like.
  • the ratio of monomers for the copolymerization may be arbitrarily determined.
  • Vinyl acetate copolymers copolymers with acrylic esters, vinyl ethers, ethylene, vinyl chloride and the like.
  • Polyvinyl ethers polyvinyl methyl ether, polyvinyl ethyl ether, polyvinyl butyl ether and the like.
  • Polyamides homonylons such as nylon 6, nylon 6-6, nylon 6-10, nylon 6-12, nylon 9, nylon 11, nylon 12, nylon 12 (tradenames) and the like, copolymers such as nylon 6/6-6/6-10, nylon 6/56-6/12. nylon 6/6-6/11 (tradenames) and the like, and modified nylons, if desired.
  • Polyesters polycondensates or copolycondensates of various dibasic acids including aliphatic dibasic acids such as oxalic acid, succinic acid, maleic acid, adipic acid, sebacic acid and the like and aromatic dibasic acids such as isophthalic acid, terephthalic acid and the like and glycols such as ethylene glycol, tetramethylene glycol, hexamethylene glycol and the like are preferred.
  • dibasic acids including aliphatic dibasic acids such as oxalic acid, succinic acid, maleic acid, adipic acid, sebacic acid and the like and aromatic dibasic acids such as isophthalic acid, terephthalic acid and the like and glycols such as ethylene glycol, tetramethylene glycol, hexamethylene glycol and the like are preferred.
  • polycondensates of aliphatic dibasic acids and glycols and copolycondenstates of glycols and aliphatic dibasic acids are more preferable.
  • a modified glyptal resin (polycondensate of phthalic anhydride and glycerine is modified by esterification with fatty acids or natural resins.) is also preferably used.
  • Polyvinyl formal and polyvinyl acetal resins which are obtained by acetalization of polyvinyl alcohol are all preferably used.
  • the degree of acetalization of the polyvinyl acetal resin may be arbitrarily determined.
  • Polyurethane resins thermoplastic polyurethane resins having urethane bonds.
  • Polyurethane resins obtained by condensation between glycols and diisocyanates and, particularly, polyurethane resins obtained by condensation between alkylene glycols and alkylene diisocyanates are preferred.
  • Polyethers styrene-formalin resins, ring-opened polymers of cyclic acetals, copolymers of polyethylene oxide and glycols, polypropylene oxide and glycols, propylene oxide-ethylene oxide, polyphenylene oxides and the like.
  • Cellulose derivatives cellulose esters and ethers such as nitro cellulose, acetyl cellulose, ethyl cellulose, acetyl butyl cellulose, hydroxyethyl cellulose, hydroxypropyl cellulose, methyl cellulose, ethylhydroxyethyl cellulose and the like, and mixtures thereof.
  • Polycarbonates various polycarbonates such as polydioxydiphenylmethane carbonate, dioxydiphenylpropane carbonate and the like.
  • Ionomers Na, Li, Zn and Mg salts of methacrylic acid and acrylic acid.
  • Ketone resins polycondenstates of cyclic ketones such as cyclohexanone, acetophenone and the like and formaldehyde.
  • Xylene resins polycondensates of m-xylene or mesitylene and formalin, or modified products thereof.
  • Petroleum resins C 5 resins, C 9 resins, C 5 -C 9 copolymers, dicyclopentadiene resins, or copolymers of these monomers or modified products thereof.
  • the metal complexes may be preferably dissolved previously in low-boiling solvent such as alkyl halides (e.g., chloroform, dichloromethane) alcohols (e.g., methanol, ethanol, isopropanol, butanol)ethers (e.g., dimethyl ether, ethyl methyl ether, diethyl ether, 1-ethoxypropane)glycols (e.g., 1,2-ethanediol, 1,2-propanediol 1,3-propanediol)ketones (e.g., acetone, ethyl metyl ketone 3-pentanone)esters (e.g., ethyl formate, methyl acetate, ethyl acetate) and amides (e.g., formamide, acetamide, succinamide).
  • alkyl halides e.g., chloroform, dichloromethan
  • the metal complex described above will bring about an improvement of the invention. Because the metal complex which is used in excess does not impede the product except that the product is objectionably colored, with respect to its upper limit the amount of the metal complex is not theoretically critical.
  • At least 0.1 mole percent of metal complex is used and an amount not less than 1 mole percent is more preferable. With the increase of amount the stabilizing effect of metal complex is enhanced. There is not any upper limit but in practice a hundred thousand moles percent or less of metal complex is used based on the organic substance.
  • UV absorbers such as Tinuvin (tradename, merchandized by CIba-Geigy AG, Swiss), hydroquinone and the like.
  • reaction operations were all effected in an argon atmosphere.
  • 23 g of sodium was cut into pieces and dispersed in 180 ml of carbon disulfide, after which 200 ml of dimethylformamide was gently added to dropwise with agitation. Care was taken in order that heat did not violently generate.
  • the mixture was gently heated with care and refluxed for 24 hours.
  • unreacted sodium was removed by filtration.
  • 50 ml of ethanol was added to the filtrate and agitated at room temperature for 2 hours.
  • the carbon disulfide was distilled off from the solution under reduced pressure at room temperature. Subsequently, into the solution 300 ml of water was gradually added dropwise, followed by subjecting the resulting solution to filtration.
  • a solution which has been prepared by dissolving 20 g of zinc chloride in 500 ml of methanol and adding 500 ml of a concentrated aqueous ammonia to the solution, was added to the above reaction solution at room temperature and agitated for 5 minutes.
  • an aqueous solution of 53 g of tetraethylammonium bromide in 250 ml of water was added, a red precipitate was immediately deposited, followed by filtration and air-drying to give the captioned zinc complex.
  • reaction operations were all effected in an argon atmosphere.
  • 25 g of sodium was cut into pieces and dispersed in 180 ml of carbon disulfide, into which 200 ml of dimethylformamide was gently added to dropwise with agitation. At that time, care was taken in order that heat did not violently generate.
  • the mixture was gently heated with care and refluxed for 24 hours.
  • unreacted sodium was removed by filtration and the carbon disulfide was distilled off from the filtrate at room temperature under reduced pressure.
  • the resulting solution was agitated on an oil bath at 140° C. for 2 hours and further agitated at room temperature or 2 hours, followed by gently adding 300 ml of water. The resulting solution was filtered.
  • a preliminarily prepared solution which was obtained by dissolving 20 g of zinc chloride in 500 ml of methanol and adding 500 ml of a concentrated aqueous ammonia to the solution, was added to the above reaction solution at room temperature and agitated for 5 minutes.
  • an aqueous solution of 53 g of tetraethylammonium bromide in 250 ml of water was added, a red precipitate was immediately deposited. The precipitate was separated by filtration followed by air-drying to give the captioned zinc complex.
  • Dimethylformamide solutions (20 ml) of various kinds of base dyes in presence of metal complexes were subjected to a fading test. Prior to light irradiation, these solutions had 2 ⁇ 10 -4 moles of base dyes and 6 ⁇ 10 -4 moles of metal complexes dissolved therein.
  • UV cut-filter Exposure time was 200 hours.
  • compositions containing the respective ingredients as shown below were prepared. After mixing the ingredients, they were subjected to filtration and applied onto a metallic support by casting to form a film respectively, and each film was peeled to give a 25 ⁇ m thick film.
  • the resultant films were each irradiated with a xenon lamp (200,000 luxes) to determine a residual rate of the dye.

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US07/006,364 1986-01-24 1987-01-23 Method for stabilizing organic base substances to light Expired - Lifetime US4761181A (en)

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JP61013396A JPS62174741A (ja) 1986-01-24 1986-01-24 有機基体物質を光に対して安定化する方法
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Cited By (53)

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US4914001A (en) * 1986-10-20 1990-04-03 Fuji Photo Film Co., Ltd. Optical information recording medium
US4921317A (en) * 1984-07-16 1990-05-01 Fuji Photo Film Co., Ltd. Infrared absorbent comprising a metal complex compound containing two thiolato bidentate ligands
US4968593A (en) * 1987-02-27 1990-11-06 Fuji Photo Film Co., Ltd. Optical information recording medium
US4981773A (en) * 1987-09-14 1991-01-01 Fuji Photo Film Co., Ltd. Method for stabilization of organic base substances against light
US4994343A (en) * 1987-06-09 1991-02-19 Fuji Photo Film Co., Ltd. Optical information recording medium
US4999281A (en) * 1987-08-20 1991-03-12 Fuji Photo Film Co., Ltd. Optical information recording medium
US5024923A (en) * 1987-09-09 1991-06-18 Fuji Photo Film Co., Ltd. Infrared absorbent compositions
US5182186A (en) * 1987-09-29 1993-01-26 Fuji Photo Film Co., Ltd. Optical information recording medium
US5616443A (en) 1993-08-05 1997-04-01 Kimberly-Clark Corporation Substrate having a mutable colored composition thereon
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JPH0588809B2 (enrdf_load_stackoverflow) 1993-12-24

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